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Synthesis 2025; 57(07): 1313-1318
DOI: 10.1055/s-0043-1773517
DOI: 10.1055/s-0043-1773517
paper
Synthesis of the Tetrasaccharide Repeating Unit Corresponding to the O-Antigen of Providencia alcalifaciens O7:H7 Strain
A.R. thanks the Council of Scientific and Industrial Research (CSIR), India for financial support. This work was supported by the Bose Institute (Department of Science and Technology, India) (A.K.M.).
Abstract
Synthesis of the tetrasaccharide corresponding to the O-antigen of Providencia alcalifaciens O7:H7 strain was achieved in satisfactory yield by applying a stereoselective glycosylation strategy. Stereoselective incorporation of β-l-rhamnose, α-d-glucosamine and α-d-glucose moieties in the tetrasaccharide was achieved in very good yield. The d-glucuronic acid moiety in the tetrasaccharide was achieved by late-stage TEMPO–bis(acetoxy)iodobenzene (BAIB)-mediated regioselective oxidation of the primary hydroxyl group of the d-glucose moiety. Thioglycosides were used as glycosyl donors in the presence of a combination of N-iodosuccinimide (NIS) and triflic acid (TfOH) as thiophilic promoter.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1773517.
- Supporting Information
Publication History
Received: 05 December 2024
Accepted after revision: 23 December 2024
Article published online:
10 February 2025
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